Cyanogen azide
Chemical compound
From Wikipedia, the free encyclopedia
Cyanogen azide is a chemical compound with the chemical formula CN4, or more precisely −N=N+=N−C≡N. It is an azide compound of carbon and nitrogen. It is an oily, colourless liquid at room temperature.[2] It is a highly explosive chemical that is soluble in most organic solvents, and normally handled in dilute solution in this form.[2][3][4] It was first synthesised by F. D. Marsh at DuPont in the early 1960s.[2][5] There had been earlier claims of discovering it as a crystalline solid, which were incorrect.[6]
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| Names | |
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| Preferred IUPAC name
Carbononitridic azide[1] | |
| Other names
Cyano azide | |
| Identifiers | |
3D model (JSmol) |
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| UNII | |
CompTox Dashboard (EPA) |
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| Properties | |
| N3CN | |
| Molar mass | 68.039 g·mol−1 |
| Appearance | Colourless oily liquid |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Cyanogen azide is a primary explosive, although it is far too unstable for practical use as an explosive and is extremely dangerous outside dilute solution.[7][8] Its use in chemistry has been as a reagent prepared in situ for use in the synthesis of chemicals such as diaminotetrazoles, either in dilute solution or as a gas at reduced pressure.[9][10][11][6][12][13][14] It can be synthesised at below room temperature from the reaction of sodium azide with either cyanogen chloride[2] or cyanogen bromide,[5] dissolved in a solvent such as acetonitrile; this reaction must be done with care due to the production of shock-sensitive byproducts from trace moisture.[5][12]